EA009620B1 - Производные 2,3,6-тризамещённого-4-пиримидона - Google Patents
Производные 2,3,6-тризамещённого-4-пиримидона Download PDFInfo
- Publication number
- EA009620B1 EA009620B1 EA200501516A EA200501516A EA009620B1 EA 009620 B1 EA009620 B1 EA 009620B1 EA 200501516 A EA200501516 A EA 200501516A EA 200501516 A EA200501516 A EA 200501516A EA 009620 B1 EA009620 B1 EA 009620B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methyl
- pyrimidin
- group
- piperazin
- pyridyl
- Prior art date
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- -1 2,3,6-trisubstituted-4-pyrimidone Chemical class 0.000 title claims description 112
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 36
- 201000010099 disease Diseases 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 34
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 239000012453 solvate Substances 0.000 claims abstract description 21
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 17
- 150000008318 pyrimidones Chemical class 0.000 claims abstract description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 11
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 10
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
- 108010061506 tau-protein kinase Proteins 0.000 claims abstract description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 7
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 70
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 53
- 239000003814 drug Substances 0.000 claims description 32
- SDGRZZUCGRBQNM-UHFFFAOYSA-N 3-methyl-6-pyridin-4-yl-2-[3-[4-(pyrrolidin-1-ylmethyl)phenyl]piperidin-1-yl]pyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(CCC2)C=2C=CC(CN3CCCC3)=CC=2)=NC=1C1=CC=NC=C1 SDGRZZUCGRBQNM-UHFFFAOYSA-N 0.000 claims description 21
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000004480 active ingredient Substances 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000003277 amino group Chemical group 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 14
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
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- 206010034010 Parkinsonism Diseases 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 9
- 206010028980 Neoplasm Diseases 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000001624 naphthyl group Chemical group 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 7
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- YIWVNLZPRGDUCN-UHFFFAOYSA-N 2-[3-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound COC1=CC(F)=CC=C1C1NCCN(C=2N(C(=O)C=C(N=2)C=2N=CN=CC=2)C)C1 YIWVNLZPRGDUCN-UHFFFAOYSA-N 0.000 claims description 5
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- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 claims description 5
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- MPZFBNGFODYXSL-UHFFFAOYSA-N 2-[3-(2,4-dimethoxyphenyl)piperazin-1-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(OC)=CC=C1C1NCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 MPZFBNGFODYXSL-UHFFFAOYSA-N 0.000 claims description 4
- RPIKXGUGTPFFLU-UHFFFAOYSA-N 2-[3-(4-fluoro-2-methoxyphenyl)piperazin-1-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound COC1=CC(F)=CC=C1C1NCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 RPIKXGUGTPFFLU-UHFFFAOYSA-N 0.000 claims description 4
- UJEZKRJUBHZWII-UHFFFAOYSA-N 2-[3-(4-methoxyphenyl)piperazin-1-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C1=CC(OC)=CC=C1C1NCCN(C=2N(C(=O)C=C(N=2)C=2C=CN=CC=2)C)C1 UJEZKRJUBHZWII-UHFFFAOYSA-N 0.000 claims description 4
- YSRSQVSJNOMEFR-UHFFFAOYSA-N 2-[4-(6-fluoro-1-benzothiophen-3-yl)piperidin-1-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CCC(CC2)C=2C3=CC=C(F)C=C3SC=2)=NC=1C1=CC=NC=N1 YSRSQVSJNOMEFR-UHFFFAOYSA-N 0.000 claims description 4
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- 210000003719 b-lymphocyte Anatomy 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
- 125000005170 cycloalkyloxycarbonyl group Chemical group 0.000 claims description 4
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- 208000032839 leukemia Diseases 0.000 claims description 4
- 125000006413 ring segment Chemical group 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- UXHXFNYENJPKFQ-UHFFFAOYSA-N 2-[3-(1,2-benzoxazol-3-yl)piperidin-1-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(CCC2)C=2C3=CC=CC=C3ON=2)=NC=1C1=CC=NC=N1 UXHXFNYENJPKFQ-UHFFFAOYSA-N 0.000 claims description 3
- KDHZHPBJALIJJU-UHFFFAOYSA-N 2-[3-(2,6-dichlorophenyl)piperazin-1-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(NCC2)C=2C(=CC=CC=2Cl)Cl)=NC=1C1=CC=NC=C1 KDHZHPBJALIJJU-UHFFFAOYSA-N 0.000 claims description 3
- GOOSNFHJOVCMSO-UHFFFAOYSA-N 2-[3-(4-chlorophenyl)piperazin-1-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(NCC2)C=2C=CC(Cl)=CC=2)=NC=1C1=CC=NC=N1 GOOSNFHJOVCMSO-UHFFFAOYSA-N 0.000 claims description 3
- NLFRUPSAGIMPEK-UHFFFAOYSA-N 2-pyridin-4-yl-1h-pyrimidin-6-one Chemical compound OC1=CC=NC(C=2C=CN=CC=2)=N1 NLFRUPSAGIMPEK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
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- RWFVIDMRNJSYQE-UHFFFAOYSA-N 1-(1-methyl-6-oxo-4-pyrimidin-4-ylpyrimidin-2-yl)-4-phenylpiperidine-4-carbonitrile Chemical compound C=1C(=O)N(C)C(N2CCC(CC2)(C#N)C=2C=CC=CC=2)=NC=1C1=CC=NC=N1 RWFVIDMRNJSYQE-UHFFFAOYSA-N 0.000 claims description 2
- FXLWUBJQAGRTRG-UHFFFAOYSA-N 2-(3-hydroxy-3-phenylpiperidin-1-yl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(O)(CCC2)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 FXLWUBJQAGRTRG-UHFFFAOYSA-N 0.000 claims description 2
- GZAPRCPGNZCHMI-UHFFFAOYSA-N 2-(4-benzoylpiperazin-1-yl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CCN(CC2)C(=O)C=2C=CC=CC=2)=NC=1C1=CC=NC=C1 GZAPRCPGNZCHMI-UHFFFAOYSA-N 0.000 claims description 2
- XZGNYXGHOLGXNS-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CCN(CC=3C=CC=CC=3)CC2)=NC=1C1=CC=NC=C1 XZGNYXGHOLGXNS-UHFFFAOYSA-N 0.000 claims description 2
- JYKICDOEUQZCBI-UHFFFAOYSA-N 2-[3-(1-benzofuran-2-yl)piperazin-1-yl]-3-methyl-6-pyridin-4-ylpyrimidin-4-one Chemical compound C=1C(=O)N(C)C(N2CC(NCC2)C=2OC3=CC=CC=C3C=2)=NC=1C1=CC=NC=C1 JYKICDOEUQZCBI-UHFFFAOYSA-N 0.000 claims description 2
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- KWDFPPZIPCYCDL-UHFFFAOYSA-N 2-[3-(2,5-dimethoxyphenyl)piperazin-1-yl]-3-methyl-6-pyrimidin-4-ylpyrimidin-4-one Chemical compound COC1=CC=C(OC)C(C2NCCN(C2)C=2N(C(=O)C=C(N=2)C=2N=CN=CC=2)C)=C1 KWDFPPZIPCYCDL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Ophthalmology & Optometry (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2003126022 | 2003-03-26 | ||
| JP2003126021 | 2003-03-26 | ||
| PCT/JP2004/004320 WO2004085408A1 (en) | 2003-03-26 | 2004-03-26 | 2, 3, 6-trisubstituted-4-pyrimidone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200501516A1 EA200501516A1 (ru) | 2006-04-28 |
| EA009620B1 true EA009620B1 (ru) | 2008-02-28 |
Family
ID=33100427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200501516A EA009620B1 (ru) | 2003-03-26 | 2004-03-26 | Производные 2,3,6-тризамещённого-4-пиримидона |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7504411B2 (pt) |
| EP (3) | EP2305651A1 (pt) |
| JP (1) | JP4679509B2 (pt) |
| KR (1) | KR100985419B1 (pt) |
| CN (1) | CN1764650B (pt) |
| AR (1) | AR045677A1 (pt) |
| AU (1) | AU2004223987B2 (pt) |
| BR (1) | BRPI0409042A (pt) |
| CA (1) | CA2520027C (pt) |
| EA (1) | EA009620B1 (pt) |
| IL (1) | IL170877A (pt) |
| NO (1) | NO20054952L (pt) |
| NZ (1) | NZ543096A (pt) |
| TW (1) | TWI357408B (pt) |
| WO (1) | WO2004085408A1 (pt) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI241298B (en) | 1998-09-25 | 2005-10-11 | Mitsubishi Chem Corp | Pyrimidone derivatives |
| AU2002337499B2 (en) | 2001-09-21 | 2007-08-23 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
| KR100754596B1 (ko) | 2001-09-21 | 2007-09-05 | 미쯔비시 웰 파마 가부시키가이샤 | 3-치환-4-피리미돈 유도체 |
| MXPA05006394A (es) * | 2002-12-16 | 2007-04-16 | Mitsubishi Pharma Corp | Derivados de 4-pirimidona 3-sustituida. |
| US7550590B2 (en) | 2003-03-25 | 2009-06-23 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| KR20060041309A (ko) | 2003-08-13 | 2006-05-11 | 다케다 야쿠힌 고교 가부시키가이샤 | 4-피리미돈 유도체 및 펩티딜 펩티다제 저해제로서의 그의용도 |
| US7790734B2 (en) | 2003-09-08 | 2010-09-07 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| GB0325956D0 (en) | 2003-11-06 | 2003-12-10 | Addex Pharmaceuticals Sa | Novel compounds |
| CN102127057A (zh) | 2004-03-15 | 2011-07-20 | 武田药品工业株式会社 | 二肽基肽酶抑制剂 |
| AR050865A1 (es) * | 2004-09-09 | 2006-11-29 | Sanofi Aventis | Derivados de 2- morfolino-4-pirimidona |
| PT1805164E (pt) * | 2004-09-29 | 2011-04-11 | Sanofi Aventis | Derivados de 6-(piridinil)-4-pirimidona como inibidores de proteína-cinase tau 1 |
| EP1802587A4 (en) * | 2004-10-15 | 2010-02-17 | Astrazeneca Ab | SUBSTITUTED AMINO BINDINGS AND THEIR APPLICATIONS |
| WO2006041405A1 (en) * | 2004-10-15 | 2006-04-20 | Astrazeneca Ab | Substituted amino-pyrimidones and uses thereof |
| CN101115726A (zh) * | 2004-12-03 | 2008-01-30 | 先灵公司 | 作为cb1拮抗剂的取代哌嗪 |
| WO2006068978A2 (en) | 2004-12-21 | 2006-06-29 | Takeda Pharmaceutial Company Limited | Dipeptidyl peptidase inhibitors |
| TW200740779A (en) * | 2005-07-22 | 2007-11-01 | Mitsubishi Pharma Corp | Intermediate compound for synthesizing pharmaceutical agent and production method thereof |
| GEP20135838B (en) | 2005-09-14 | 2013-06-10 | Takeda Pharmaceutical | Dipeptidyl peptidase inhibitors usage at diabetes treatment |
| CN101360723A (zh) | 2005-09-16 | 2009-02-04 | 武田药品工业株式会社 | 制备嘧啶二酮衍生物的方法 |
| TW200813015A (en) * | 2006-03-15 | 2008-03-16 | Mitsubishi Pharma Corp | 2-(cyclic amino)-pyrimidone derivatives |
| US20100292205A1 (en) * | 2006-08-23 | 2010-11-18 | Pfizer Inc. | Pyrimidone Compounds As GSK-3 Inhibitors |
| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
| TW200838536A (en) | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
| AR064660A1 (es) * | 2006-12-26 | 2009-04-15 | Mitsubishi Tanabe Pharma Corp | Derivados de pirimidinona 6-heterociclica 2-sustituida, medicamentos que los contienen y usos para prevenir y/o tratar enfermedades neurodegenerativas entre otras |
| EP2119709A4 (en) | 2007-02-09 | 2011-08-17 | Kaneka Corp | PROCESS FOR PREPARING OPTICALLY ACTIVE 2-ARYLPIPERAZINE DERIVATIVE |
| US8093236B2 (en) | 2007-03-13 | 2012-01-10 | Takeda Pharmaceuticals Company Limited | Weekly administration of dipeptidyl peptidase inhibitors |
| US8623873B2 (en) * | 2007-06-28 | 2014-01-07 | Intervet Inc. | Substituted piperazines as CB1 antagonists |
| JP2010531360A (ja) * | 2007-06-28 | 2010-09-24 | インターベット インターナショナル ベー. フェー. | Cb1拮抗剤としてのピペラジンの使用 |
| AU2008297817A1 (en) | 2007-09-14 | 2009-03-19 | Mitsubishi Tanabe Pharma Corporation | 6-pyrimidinyl-pyrimid-4-one derivative |
| WO2011019089A1 (en) * | 2009-08-13 | 2011-02-17 | Mitsubishi Tanabe Pharma Corporation | Pyrimidone derivatives used as tau protein kinase 1 inhibitors |
| WO2011019090A1 (en) | 2009-08-13 | 2011-02-17 | Mitsubishi Tanabe Pharma Corporation | Pyrimidone derivatives used as tau protein kinase 1 inhibitors |
| CN104211635A (zh) * | 2013-06-03 | 2014-12-17 | 中国科学院上海药物研究所 | 一类哌啶类化合物及其制备方法、药物组合物和用途 |
| US10246463B2 (en) | 2015-04-07 | 2019-04-02 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Hypoxia-inducible factor 1 (HIF-1) inhibitors |
| CN105130904B (zh) * | 2015-08-24 | 2017-10-13 | 如东众意化工有限公司 | 一种2‑氰基‑4‑氯‑5‑(4‑甲基苯基)咪唑的合成方法 |
| CN106854189A (zh) * | 2015-12-08 | 2017-06-16 | 湖南华腾制药有限公司 | 一种哌嗪化合物的合成方法 |
| CN121843926A (zh) * | 2023-06-16 | 2026-04-10 | 跨神经元治疗公司 | 5-ht2a受体调节剂及其使用方法 |
| CN119841766B (zh) * | 2025-01-16 | 2025-12-12 | 上海凌凯科技股份有限公司 | 一种戊二酰亚胺类化合物的制备方法及应用 |
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| EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
| WO2003027080A1 (en) * | 2001-09-21 | 2003-04-03 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
| WO2003037888A1 (en) * | 2001-09-21 | 2003-05-08 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
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| JP4064671B2 (ja) | 2000-02-25 | 2008-03-19 | エフ.ホフマン−ラ ロシュ アーゲー | アデノシン受容体モジュレーター |
| FR2806723B1 (fr) | 2000-03-23 | 2002-05-10 | Sanofi Synthelabo | DERIVES D'ACIDE 8-OXO-5,8-DIHYDRO-6H-DIBENZO [a,g] QUINOLIZINE-13-PROPANOIQUE , LEUR PREPARATION ET LEUR APPLICATION EN THERAPEUTIQUE |
| WO2001070728A1 (en) | 2000-03-23 | 2001-09-27 | Sanofi-Synthelabo | 2-[nitrogen-heterocyclic]pyrimidone derivatives |
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-
2004
- 2004-03-25 TW TW093108174A patent/TWI357408B/zh not_active IP Right Cessation
- 2004-03-26 EA EA200501516A patent/EA009620B1/ru not_active IP Right Cessation
- 2004-03-26 EP EP10192295A patent/EP2305651A1/en not_active Withdrawn
- 2004-03-26 EP EP04723777A patent/EP1608630A1/en not_active Withdrawn
- 2004-03-26 CA CA2520027A patent/CA2520027C/en not_active Expired - Fee Related
- 2004-03-26 CN CN2004800080655A patent/CN1764650B/zh not_active Expired - Fee Related
- 2004-03-26 JP JP2006507692A patent/JP4679509B2/ja not_active Expired - Fee Related
- 2004-03-26 BR BRPI0409042-0A patent/BRPI0409042A/pt not_active IP Right Cessation
- 2004-03-26 EP EP10192283A patent/EP2308854A1/en not_active Withdrawn
- 2004-03-26 WO PCT/JP2004/004320 patent/WO2004085408A1/en not_active Ceased
- 2004-03-26 AU AU2004223987A patent/AU2004223987B2/en not_active Ceased
- 2004-03-26 AR ARP040101028A patent/AR045677A1/es not_active Application Discontinuation
- 2004-03-26 KR KR1020057017840A patent/KR100985419B1/ko not_active Expired - Fee Related
- 2004-03-26 US US10/550,299 patent/US7504411B2/en not_active Expired - Fee Related
- 2004-03-26 NZ NZ543096A patent/NZ543096A/en not_active IP Right Cessation
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2005
- 2005-09-15 IL IL170877A patent/IL170877A/en not_active IP Right Cessation
- 2005-10-25 NO NO20054952A patent/NO20054952L/no not_active Application Discontinuation
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1136482A1 (en) * | 2000-03-23 | 2001-09-26 | Sanofi-Synthelabo | 2-Amino-3-(alkyl)-pyrimidone derivatives as GSK3beta inhibitors |
| WO2003027080A1 (en) * | 2001-09-21 | 2003-04-03 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
| WO2003037888A1 (en) * | 2001-09-21 | 2003-05-08 | Mitsubishi Pharma Corporation | 3-substituted-4-pyrimidone derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1764650A (zh) | 2006-04-26 |
| US7504411B2 (en) | 2009-03-17 |
| EP2308854A1 (en) | 2011-04-13 |
| AR045677A1 (es) | 2005-11-09 |
| IL170877A (en) | 2011-02-28 |
| BRPI0409042A (pt) | 2006-03-28 |
| KR100985419B1 (ko) | 2010-10-05 |
| JP4679509B2 (ja) | 2011-04-27 |
| CN1764650B (zh) | 2010-06-16 |
| CA2520027A1 (en) | 2004-10-07 |
| WO2004085408A1 (en) | 2004-10-07 |
| HK1090368A1 (zh) | 2006-12-22 |
| AU2004223987A1 (en) | 2004-10-07 |
| CA2520027C (en) | 2011-08-09 |
| NO20054952L (no) | 2005-10-25 |
| JP2006521370A (ja) | 2006-09-21 |
| EP1608630A1 (en) | 2005-12-28 |
| TWI357408B (en) | 2012-02-01 |
| TW200510338A (en) | 2005-03-16 |
| US20060252768A1 (en) | 2006-11-09 |
| NZ543096A (en) | 2008-07-31 |
| EA200501516A1 (ru) | 2006-04-28 |
| AU2004223987B2 (en) | 2010-02-18 |
| KR20050111613A (ko) | 2005-11-25 |
| EP2305651A1 (en) | 2011-04-06 |
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| MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
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